Vacation Rentals with Pool in Kaupulehu, HI: Compare 10+ Sites & Save

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  2. Vacation Rentals with Pool
  3.  USA

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  5.  Kailua-Kona

  6.  Kaupulehu

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64 Best Vacation Rentals with Pool in Kaupulehu (Starting from $582)

3BD Hainoa Villa (2907C) at Hualalai Resort
3BD Hainoa Villa (2907C) at Hualalai Resort
Villa
Kukio, HI, USA
0.3k from Kaupulehu center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$2044
Average price / night
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Laueki 8 – Stunning Ocean View | Onsite Staff & Daily Housekeeping
Laueki 8 – Stunning Ocean View | Onsite Staff & Daily Housekeeping
House
Kailua Kona, HI, 96740, United States
0.1k from Kaupulehu center

AC, Dryer, Free Parking, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space, Patio

4 Bedrooms8 Guests
New to Booking
$8527
Average price / night
Check Availability
4BD Ke Alaula Estate (124) at Hualalai Resort
4BD Ke Alaula Estate (124) at Hualalai Resort
Villa
Kukio, HI, USA
0.5k from Kaupulehu center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Hot tubs, Places to stay

4 Bedrooms8 Guests
New to Booking
$4321
Average price / night
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Laueki 5 – Ocean View Estate | Onsite Staff & Daily Housekeeping
Laueki 5 – Ocean View Estate | Onsite Staff & Daily Housekeeping
House
Kailua Kona, HI, 96740, United States
0.1k from Kaupulehu center

AC, Barbecue, Dryer, Kitchen, Laundry, Living Area, Microwave, No Smoking, Patio

5 Bedrooms10 Guests
New to Booking
$9330
Average price / night
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3BD Ka'Ulu Villa (131C) at Hualalai Resort
3BD Ka'Ulu Villa (131C) at Hualalai Resort
Villa
Kukio, HI, USA
0.7k from Kaupulehu center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Hot tubs, Places to stay

3 Bedrooms6 Guests
New to Booking
$1684
Average price / night
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Golf lovers delight Lau'eki ~ Hualalai ~ Sweeping Views
Golf lovers delight Lau'eki ~ Hualalai ~ Sweeping Views
House
Kailua Kona, HI, 96740, United States
0.1k from Kaupulehu center

AC, Barbecue, Breakfast Available, Crib, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet

4 Bedrooms8 Guests
10.0

Exceptional

7 reviews

$5308
Average price / night
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Four Seasons Resort Hualalai
Four Seasons Resort Hualalai
Resort
Kaupulehu, HI, USA
1.4k from Kaupulehu center

Luxury, Accommodations, Pools, Resorts, Parking, Spa, Pet-friendly, 5-star, Lodgings

185 Bedrooms63 Guests
9.5

Superb

37 reviews

$1440
Average price / night
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Luxury Estate at Hualalai Resort -Sweeping Ocean and Golf Course Views
Luxury Estate at Hualalai Resort -Sweeping Ocean and Golf Course Views
House
Kailua Kona, HI, 96740, United States
0.2k from Kaupulehu center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area

5 Bedrooms10 Guests
New to Booking
$7355
Average price / night
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Kona Village A Rosewood Resort
Kona Village A Rosewood Resort
Resort
Kailua-Kona, HI, USA
1.9k from Kaupulehu center

Luxury, Accommodations, Pools, Resorts, Parking, Spa, Pet-friendly, Lodgings, Beach

150 Bedrooms207 Guests
8.9

Fabulous

17 reviews

$1555
Average price / night
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Hualalai Hainoa Estate | private residence | pool | panoramic ocean views
Hualalai Hainoa Estate | private residence | pool | panoramic ocean views
House
Kailua-Kona, HI, 96740, United States
0.2k from Kaupulehu center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
9.4

Superb

3 reviews

$3737
Average price / night
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Hualalai Fairway Villa
Hualalai Fairway Villa
Villa
Kukio, HI, USA
2.4k from Kaupulehu center

Parking, Internet, Air Conditioner, Pool, Child Friendly

3 Bedrooms8 Guests
New to Booking
$582
Average price / night
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Designer Oceanview Estate w/Pool & Spa, at Hualalai Resort: 122 Hainoa
Designer Oceanview Estate w/Pool & Spa, at Hualalai Resort: 122 Hainoa
House
Kailua Kona, HI, 96740, United States
0.2k from Kaupulehu center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking

4 Bedrooms8 Guests
10.0

Exceptional

7 reviews

$3316
Average price / night
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Hainoa 10 – Commanding Ocean Views | Onsite Staff & Daily Housekeeping
Hainoa 10 – Commanding Ocean Views | Onsite Staff & Daily Housekeeping
House
Kailua Kona, HI, 96740, United States
0.3k from Kaupulehu center

AC, Dryer, Free Parking, Kitchen, Laundry, Living Area, Microwave, No Smoking, Patio

3 Bedrooms6 Guests
New to Booking
$7125
Average price / night
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Premier Hualalai Resort Estate | Special Pricing | Includes Chef Experience
Premier Hualalai Resort Estate | Special Pricing | Includes Chef Experience
House
Kailua-Kona, HI, 96740, United States
0.3k from Kaupulehu center

AC, Breakfast Available, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

5 Bedrooms10 Guests
New to Booking
$8054
Average price / night
Check Availability
Ultra Luxe Oceanview Estate at Hualalai, Private Pool & Spa: 102 Hainoa
Ultra Luxe Oceanview Estate at Hualalai, Private Pool & Spa: 102 Hainoa
House
Kailua Kona, HI, 96740, United States
0.3k from Kaupulehu center

AC, Balcony, Barbecue, Dryer, Free Parking, Hot Tub, Kitchen, Laundry, Microwave

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$4224
Average price / night
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Ke Alaula Estate: Hualalai Luxury w/Lanai, Heated Pool & Golf Views
Ke Alaula Estate: Hualalai Luxury w/Lanai, Heated Pool & Golf Views
House
Kailua Kona, HI, 96740, United States
0.5k from Kaupulehu center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Hot Tub, Kitchen, Laundry

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$3526
Average price / night
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Ultra Luxurious New Home in Four Seasons Hualalai
Ultra Luxurious New Home in Four Seasons Hualalai
House
Kailua-Kona, HI, 96740, United States
0.6k from Kaupulehu center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

6 Bedrooms14 Guests
10.0

Exceptional

6 reviews

$8730
Average price / night
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Ke Alaula Hale 7 – Private & Secluded | Onsite Staff & Daily Housekeeping
Ke Alaula Hale 7 – Private & Secluded | Onsite Staff & Daily Housekeeping
House
Kailua Kona, HI, 96740, United States
0.6k from Kaupulehu center

AC, Dryer, Free Parking, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space, Pool

3 Bedrooms6 Guests
New to Booking
$5138
Average price / night
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Premier 5BR Hualalai Estate—Infinity Pool, 2 Golf Carts, Ocean Vistas
Premier 5BR Hualalai Estate—Infinity Pool, 2 Golf Carts, Ocean Vistas
House
Kailua Kona, HI, 96740, United States
0.6k from Kaupulehu center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Hot Tub, Kitchen, Microwave

5 Bedrooms10 Guests
New to Booking
$4203
Average price / night
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FOUR SEASONS RESORT \"HUALALAI HALE” MODERN OCEANVIEW, 7 & 28- SPECIAL NIGHT RATE
FOUR SEASONS RESORT \"HUALALAI HALE” MODERN OCEANVIEW, 7 & 28- SPECIAL NIGHT RATE
House
Kailua Kona, HI, 96740, United States
0.6k from Kaupulehu center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
10.0

Exceptional

78 reviews

$3958
Average price / night
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Luxurious & Serene Home w/ Private Pool & Spa
Luxurious & Serene Home w/ Private Pool & Spa
House
Kailua-Kona, HI, 96740, United States
0.6k from Kaupulehu center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

4 Bedrooms10 Guests
10.0

Exceptional

7 reviews

$5188
Average price / night
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Pohinahina Hale – Modern & Private | Onsite Staff & Daily Housekeeping
Pohinahina Hale – Modern & Private | Onsite Staff & Daily Housekeeping
House
Kailua Kona, HI, 96740, United States
0.7k from Kaupulehu center

AC, Dryer, Free Parking, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space, Patio

5 Bedrooms10 Guests
New to Booking
$9045
Average price / night
Check Availability
Piiuka 18 - Ocean Views | Game Room | Daily Housekeeping
Piiuka 18 - Ocean Views | Game Room | Daily Housekeeping
House
Kailua Kona, HI, 96740, United States
0.7k from Kaupulehu center

AC, Dryer, Kitchen, Living Area, Microwave, No Smoking, Pool, Washer

6 Bedrooms12 Guests
New to Booking
$11136
Average price / night
Check Availability
Golf Villa 5102 - Best Ocean Views | Daily Housekeeping
Golf Villa 5102 - Best Ocean Views | Daily Housekeeping
House
Kailua Kona, HI, 96740, United States
0.7k from Kaupulehu center

AC, Dryer, Kitchen, Living Area, Microwave, No Smoking, Patio, Pool, Washer

3 Bedrooms6 Guests
New to Booking
$4779
Average price / night
Check Availability
Beautiful Fairway Villa 104A at Hualalai w/Resort Pool, AC & Two Golf Carts
Beautiful Fairway Villa 104A at Hualalai w/Resort Pool, AC & Two Golf Carts
Condo
Kailua Kona, HI, 96740, United States
0.7k from Kaupulehu center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Hot Tub, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

15 reviews

$1740
Average price / night
Check Availability
Four Seasons Resort Hualalai at 4th Fairway, Ocean View with 2 Golf Carts
Four Seasons Resort Hualalai at 4th Fairway, Ocean View with 2 Golf Carts
Villa
Kailua-Kona, HI, 96740, United States
0.7k from Kaupulehu center

AC, Arcade, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub

3 Bedrooms6 Guests
10.0

Exceptional

46 reviews

$2038
Average price / night
Check Availability
Double-Level Infinity Pool & Spa | Hualalai Resort | Includes Chef Experience
Double-Level Infinity Pool & Spa | Hualalai Resort | Includes Chef Experience
Villa
Kailua-Kona, HI, 96740, United States
0.7k from Kaupulehu center

AC, Breakfast Available, Crib, Dryer, Free Parking, Heater, Housekeeping, Internet, Kitchen

4 Bedrooms8 Guests
New to Booking
$14008
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals with Pool in Kaupulehu.

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Kaupulehu Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 64 verified vacation rentals with a pool in Kaupulehu. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Kaupulehu vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $582 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Kaupulehu offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Kaupulehu welcome pets. Currently, 3 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Kaupulehu often include additional outdoor features such as Pool, Laundry, and Internet. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Kaupulehu offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.